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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Oakham holiday rentals

A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

1. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is £588
includes taxes & fees
10 Nov - 11 Nov
The Christmas Cottage, 4BR New England Escape
The Cottage is nestled next to the historic Sagendorph Mansion.

2. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is £199
includes taxes & fees
2 Nov - 3 Nov
Cottage by the Castle – Downtown Spencer
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

3. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
9.0 out of 10, Wonderful, (2 reviews)
"Nice and very clean. Host communicated fast and helpful."
United States
Ekaterina
The price is £89
includes taxes & fees
3 Nov - 4 Nov
Clean & Cozy Private-3 floor_R 2
A grassy outdoor area with a hammock, chairs, and a stone wall.

4. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (27 reviews)
"This was a super cozy ,cute place to stay . Host had muffins , juice and milk for us. The property was quiet and very peaceful."
United States
theresa H.
The price is £149
includes taxes & fees
3 Nov - 4 Nov
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

5. Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Westminster
10.0 out of 10, Exceptional, (37 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is £389
includes taxes & fees
11 Nov - 12 Nov
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

6. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is £187
includes taxes & fees
3 Nov - 4 Nov
Angel Sky Challenge
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

7. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (3 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is £375
includes taxes & fees
3 Nov - 4 Nov
4-bedroom house in nice Holden with WiFi, AC
A neatly made bed with rolled towels, a bedside table with a lamp, and a large mirror on the wall.

8. Newly Refreshed 3bd Spacious Unit Minutes from 290

Newly Refreshed 3bd Spacious Unit Minutes from 290
Franklin Plantation
9.4 out of 10, Exceptional, (3 reviews)
"The communication was wonderful. There were some things that needed to be addressed and they were.We would definitely rent again! The space is very spacious and clean"
United States
Anonymous traveller
The price is £184
includes taxes & fees
2 Nov - 3 Nov
Newly Refreshed 3bd Spacious Unit Minutes from 290
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

9. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (4 reviews)
"Gorgeously decorated and ultra-clean. Was the perfect rental for my sisters wedding at Salem Cross Inn"
United States
Trish N.
The price is £288
includes taxes & fees
1 Nov - 2 Nov
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A living room with a gray sofa, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted plant.

10. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is £249
includes taxes & fees
1 Nov - 2 Nov
Large 3BD 1st Floor Apartment Minutes from 290
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

11. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
3.0 star property
Worcester
The price is £340
includes taxes & fees
22 Nov - 23 Nov
Worcester Lakefront Cottage Apt w/ Shared Dock!
A living room with a TV, a sofa, a chair, a lamp, and a window with sheer curtains.

12. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
4.0 out of 10, (3 reviews)
The price is £96
includes taxes & fees
31 Oct - 1 Nov
Clean & Cozy Private room - 3 floor_R 1
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

13. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
Worcester
9.4 out of 10, Exceptional, (19 reviews)
"The host was very accommodating and responsive. Great property in a great location, would stay again!"
United States
Michaela H.
The price is £331
includes taxes & fees
22 Nov - 23 Nov
Worcester Lakefront Cottage Apt w/ Shared Dock!
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

14. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
The price is £79
includes taxes & fees
16 Nov - 17 Nov
Clean & Cozy Private- 3 floor_R 4
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

15. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
8.8 out of 10, Excellent, (3 reviews)
"Rented the property to attend a series of events at Clark University. Literally walking distance to the school so it was quite convenient. Apartment was clean, beds were comfortable. Being able to park three cars in the driveway was a huge plus as street parking near the apartment was extremely challenging. Being a Clark alum, was quite familiar with the neighborhood so I knew what to expect. Felt completely safe in the apartment as every door to the hallways had sufficient locks. We did blow a...
United States
Elyse D.
The price is £248
includes taxes & fees
1 Nov - 2 Nov
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A living room with two sofas, a coffee table, and a bookshelf.

16. Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
8.0 out of 10, Very good, (1 review)
"We did not receive information on how to enter the property until we arrived and called the owner. There was a lot of poison ivy growing in our parking area."
United States
Sharon
The price is £184
includes taxes & fees
3 Nov - 4 Nov
Heart of Shrewsbury St – 2BR Stay
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

17. Clean & Cozy Private- 3 floor_R 3

Clean & Cozy Private- 3 floor_R 3
Union HIll
The price is £96
includes taxes & fees
8 Nov - 9 Nov
Clean & Cozy Private- 3 floor_R 3
Living area

18. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is £300
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakham Hotel Reviews

Scottish Inn Sturbridge

Scottish Inn Sturbridge

10/10 Excellent
"The inn was older, but clean, quiet and nice. We would definitely stay there again."
Mary Ellen 1-night trip
Posted 1 day ago
Scottish Inn Sturbridge
The Colonial Hotel

The Colonial Hotel

8/10 Good
"This is a dated, solid 3-star hotel. The interior finishes all need a serious refresh. I was on the ground floor in a nice room, but the Wi-Fi was terrible and they stuck me down by the mechanical plant and housekeeping offices. Normally not a bid deal but they left the doors open to the mechanical room the entire time I was in my room. They also need to update the quality and number of WAPs. They were confused when I asked if they had a "business center" because they don't. Given the quality of the Wi-Fi in my room, it would've been nice if they had one.😊 The Colonial Grille is awesome; it is a shining star for this somewhat tired hotel. The restuarant/bar staff are awesome, and the food is good American fare. The bar is a lot of fun, and it's big. This is a local destination for weddings. I was there from Friday to Sunday in late October and I think there were not less than 3 weddings."
David 2-night trip
Posted 5 days ago
The Colonial Hotel

Find out more about Oakham

Everything you need to know about Oakham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakham holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakham holiday rentals we have selected for you start as low as £89 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakham rentals

At Expedia, we put the best Oakham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Oakham?

Yes, there are holiday rentals close to the most popular sights in Oakham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakham has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This holiday home rental outside of Oakham is located in a rural location, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as Great Wolf Lodge Waterpark, or get out into nature at a spot like Rock House Reservation. In the wider area, you’ll find Hardwick Vineyard and Winery and Wachusett Mountain State Reservation.

What’s a holiday rental in Oakham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakham. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family gatherings.